Why the most experienced leaders are the hardest to develop

Imagine a senior leader, twenty or twenty-five years in, receives a piece of feedback during a session. Something genuine. Something that, if it resonated, would really matter.

He pauses and nods slowly.

Says something like: “That’s really useful. I think what I’m hearing is…”

And then he reflects it back, cleanly reframed, in softer language—in a way that’s easier to hold, with less of an edge than the original.

His colleagues can see he’s engaged, not defensive. He asks a follow-up question.

It looks exactly like development.

And then the session ends, and three months later, absolutely nothing has changed in the way he leads.

The skill nobody names

The longer you’ve been in leadership, the more opportunities you’ve had to be in rooms like that one: feedback sessions, 360s, offsites, executive coaching, and leadership programs.

But if you’re like most experienced leaders, you don’t “just learn to lead” over time.

You learn to receive development. How to respond to challenges in ways that are credible, open, and professionally generous. This is rarely cynicism; it’s mostly unconscious.

But it means that by the time you have thirty years of experience, you also have thirty years of practice at the performance of being developed: the nod, the reframe, the articulate self-reflection, even the right amount of vulnerability.

It lands beautifully in the room, but it’s also why, for many leaders, nothing changes.

Why experience makes this harder

It is commonly assumed that experience makes development easier: that a senior leader has more self-awareness, more language for their own patterns, and greater capacity to use what’s offered. In some ways, that’s true.

But experience also builds fluency in the cultural performance of growth, and that fluency can become its own barrier.

When someone can articulate their edge clearly, reflect on it with precision, and receive feedback with grace, their peers tend to respond as though something has happened.

The performance of insight displaces the thing itself.

The most experienced leaders aren’t resistant to development. They’ve become fluent in its performance—and that fluency is harder to interrupt than defensiveness ever was.

What actually interrupts it

I’ve seen genuine shifts happen across twenty years of running leadership programs, and they look different from performed shifts.

And when I trace back where it started, it’s almost never in the session itself.

It’s the walk to dinner after the formal day ends, when two people end up side by side, and the conversation goes somewhere it wouldn’t have gone in the room.

Or the evening when someone orders another drink and says the thing they’d been circling around all day.

Even the morning before the program resumes, when the group is still half-present, and nobody’s quite back in role yet.

These moments aren’t accidental; they’re half the reason spending several days together works at all.

Designed content creates a starting point; the unstructured time is where something real has room to move.

Duration matters when we meet to work on ourselves, and so does “being away”—not because we can fit in more content, but because we create room for the walk, the drink, the morning coffee.

Those moments when people stop performing and start talking.

The question worth sitting with

I think about this pattern a lot, and I find myself wondering whether you recognize it—not in others, but in yourself.

Looking back at your own experience of development moments, can you tell the difference between the times something actually shifted and the times you reflected brilliantly and moved on?

I’m not sure I always can either.

— Govert

First published in the Professional Closeness Digest on 19 February 2026.